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Originally Posted by The_Jazz
Send him a copy of Penthouse Letters.
Seriously, why shouldn't his first time be the fumbling uncoordinated mess that everyone else's first time was?
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Whilst the person above has a very valid point, you could do worse than point him in the direction of my blog - which I am not sure I am supposed to do here but Im gonna do it because I just spent the last year interviewing people of all ages about their 'first times'. It might give him an idea of what he is in for. 'Caitlains Corner' - google it, is also a great source of information.
Good luck!